Photomediated synthesis of β-alkylketones from cycloalkanes

Dondi, Daniele; Cardarelli, Anna Maria; Fagnoni, Maurizio; Albini, Angelo

doi:10.1016/j.tet.2006.03.028

Cited by 66 publications

(33 citation statements)

References 54 publications

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“…3‐[(3 r ,5 r ,7 r )‐Adamantan‐1‐yl]cyclohexanone (3al): Prepared according to GPA for 28 h. The product was purified by FC (hexane/EtOAc, 97:3 to 90:10) and obtained as a pale‐yellow oil (108 mg, 0.46 mmol, 92 %). R f = 0.31 (hexane/EtOAc, 97:3).…”

Section: Methodsmentioning

confidence: 99%

Decarboxylative Giese‐Type Reaction of Carboxylic Acids Promoted by Visible Light: A Sustainable and Photoredox‐Neutral Protocol

Ramirez

González-Gómez

2017

Eur J Org Chem

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Abstract:We describe herein a transition-metal-free method for the decarboxylative generation of radicals from carboxylic acids and their 1,4-addition to Michael acceptors. The Fukuzumi catalyst (9-mesitylene-10-methylacridinium perchlorate, [AcrMes]ClO 4 ) enabled this transformation under visible-light irradiation at room temperature with CO 2 as the only byproduct. The scope and limitations of this protocol were examined by using

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Section: Methodsmentioning

confidence: 99%

Decarboxylative Giese‐Type Reaction of Carboxylic Acids Promoted by Visible Light: A Sustainable and Photoredox‐Neutral Protocol

Ramirez

González-Gómez

2017

Eur J Org Chem

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“…17 Indeed, other benzophenone derivatives (including xanthones such as XO and TXO, and fluorenone FLN) exhibit triplet quantum yields close to unity and share similar reactivity patterns. With high yielding and relatively high-lying T 1 states, benzophenones are some of the most effective mediators of triplet energy transfer, 205 211 Ultimately, reverse hydrogen atom transfer (RHAT) or reverse ET/PT is required for turnover of the ketyl radical BPH• in order for BP to be employed catalytically; however, these processes are known to occur slowly, 10 and dimerization of BPH• to benzopinacol (BPH) 2 can be problematic. 211 HAT reactivity of the type discussed here can be accomplished by other triplet excited ketones (such as acetone or acetophenone), but benzophenones have absorptions closer to the visible (∼300−380 nm), likely contributing to their preferred use as photoredox catalysts.…”

Section: Cyanoarene Catalyst Developmentmentioning

confidence: 99%

Organic Photoredox Catalysis

2016

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In this review, we highlight the use of organic photoredox catalysts in a myriad of synthetic transformations with a range of applications. This overview is arranged by catalyst class where the photophysics and electrochemical characteristics of each is discussed to underscore the differences and advantages to each type of single electron redox agent. We highlight both net reductive and oxidative as well as redox neutral transformations that can be accomplished using purely organic photoredox-active catalysts. An overview of the basic photophysics and electron transfer theory is presented in order to provide a comprehensive guide for employing this class of catalysts in photoredox manifolds.

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“…[8,10] Tetrabutylammonium decatungstate (TBADT) has been recently introduced and has been found to promote the photocatalyzed alkylation of enones, unsaturated esters and nitriles starting directly from alkanes. [11] A selective transformation was obtained through the same method in the alkylation by aliphatic alcohols and ethers [12] and in the acylation by aliphatic aldehydes. [13] We surmised that TBADT might be conveniently applied for the (chemo)selective photocatalyzed functionalization of amides.…”

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confidence: 99%